William,
I agree wholeheartedly with mtachhi's comments about having faith and confidence one is being told the truth. It all starts here. When I stayed in the W/Times SQ last March, we purposefully checked out of the Sheraton/NYC just up the road, caught a cab for a very short ride straight down the street to the W/TImes Sq...and by 10:30AM on a FRIDAY morning were checking in at the W/Times SQ...not in any way expecting to really get a room that early, per se, but planned to leave bags w/ bellman and be FIRST IN LINE for a room upgrade. Nope. Didn't happen. Not only were we told at 10:30AM no upgrades available, which of course implicitly meant ALL UPGRADES FOR THE EVENING WOULD HAVE HAD TO HAVE BEEN RESERVED WITH POINTS or at the site rates, ahead of us...but then we were given a room facing....a very unspectacular view of the Marriott Marquis across the street. And we had paid a higher rate for a "spectacular view" room or whatever they call it. Very unimpressed at that point. And I definitely felt deceived re: the suite availability issue, or at least a corner room (which I knew to ask for from having read these threads prior to my trip).
At this point rgoel's ideas would have been called for IMO...if no upgrade was available...then a corner room or one with a true view of Times Sq...would have been sufficient...or maybe an offer to comp the broadband ($15 value back then I think it was).
Instead, they half-heartedly apologized, and only after 3PM-something when they still couldn't give me a room for check-in...did they offer a 500-point bonus for the hassle (3rd time I had returned to actually go through w/ the checkin).
I should point out I was only GOLD at the time, and I realized PLATs would outrank me for upgrades after 3PM normal check-in times, which was a key reason we went to some extra effort to leave the Sheraton and get to this W by 10:30AM...if nothing else to get one of the fabled corner rooms overlooking Times.
Just one example.
So, in the order:
1) like mtachhi mentions, these property clerks MUST stop lying to our face. I would say it happens more than not.
2) Then, any of rgoel's ideas would be fair and reasonable if upgrade simply aren't available, and finally
3) uniquely, I have a strong need for broadband when on the road, so a comp of this would be agreeable to me.